Disazo dyestuffs

ABSTRACT

DISAZO DYESTUFFS OF FORMULA   6-(4-(4-(R-NH-NAPHTHVL)-N=N-)NAPHTHYL-N=N-)-   1,3-BENZODIOXAN   IN WHICH R DENOTES ALKYL GROUPS, WHICH CAN BE SUBSTITUTED BY ALKOXY RADICALS, ALKOXYCARBONYL RADICALS, NITRILE, HYDROXYL OR HALOGEN, AS WELL AS THEIR PREPARATION AND THEIR USE FOR DYEING HYDROPHOBIC FIBRE MATERIALS.

United States Patent f 3,705,145 DISAZO DYESTUFFS Alois Gottschlich andKlaus Leverenz, Leverkusen, Germany, assignors to Farbenfabriken BayerAktiengesellschaft, Leverkusen, Germany No Drawing. Filed Nov. 19, 1970,Ser. No. 91,158 Claims priority, application Germany, Nov. 28, 1969, P19 59 774.1 Int. Cl. C09b 31/04 US. Cl. 260152 14 Claims ABSTRACT OF THEDISCLOSURE Disazo dyestuffs of formula in which R denotes alkyl groups,which can be substituted by alkoxy radicals, alkoxycarbonyl radicals,nitrile, hydroxyl or halogen, as well as their preparation and their usefor dyeing hydrophobic fibre materials.

The subject of the present invention are new valuable disazo dyestuffs,free of sulphonic acid groups and carboxylic acid groups, of formula \OCH Q Q in which R represents an optionally substituted alkyl radical, aswell as their manufacture and use.

Suitable radicals R are especially alkyl groups with 1 to 4 C atomswhich can be substituted by alkoxy radicals with 1 to 4 C atoms,alkoxycarbonyl radicals with 2 to 5 C atoms, nitrile, hydroxyl orhalogen, such as fluorine,

chlorine and bromine.

The new dyestuffs of Formula I are obtained if the aminoazo dyestutf offormula o-cm is diazotised and coupled with naphthylamines of formula g(III) 3,705,145 Patented Dec. 5, 1972 1-N-methylaminonaphthalene,l-N-1-ethylamino-naphthalene,

1-N- B-hydroxyethylamino) -naphthalene, 1-N-(flhydroxypropylamino-naphthalene,

l-N- (fi-hydroxybutylarnino -naphthalene,

l-N- (fi-hydroxy-' -chloropropylamino -naphthalene, l-N-(fl-hydroxy-'y-methoxy-propylamino -naphthalene, l-N-(B-methoxycarbonylethylamino -naphthalene, and l-N- (fi-cyanethylamino-naphtha1ene The diazotisation of II can be carried out in a mannerwhich is in itself known, with the addition of dispersing agents and/orpolar organic solvents, such as ethylene glycol, ethylene glycolmonoalkyl ethers, formamide or dimethylformamide, in dilute hydrochloricacid or sulphuric acid by means of sodium nitrite solution, or inconcentrated sulphuric acid, strength o-phosphoric acid, acetic acid,propionic acid or mixtures of these acids using nitrosylsulphuric acid.

The coupling components can be employed in the form of their solutionsin dilute mineral acids, such as dilute hydrochloric acid or dilutesulphuric acid, or in organic solvents, such as methanol, ethanol,isopropanol, ethylene glycol, ethylene glycol rnonomethyl ether,ethylene glycol monoethyl ether, diethylene glycol, formamide,dimethylformamide, pyridine or acetic acid.

Diazotisation and coupling are preferably carried out in the temperaturerange of 0 to 40 C.

After completion of the coupling, the disazo dyestuffs of Formula I areisolated by filtering off, and are washed with water and dried.

The dyestuffs of Formula I obtainable in accordance with the inventionare in particular suitable for use, in a finely divided form, for thedyeing of hydrophobic fibre materials of aromatic polyesters, celluloseacetates, polyolefines, polyurethanes, polyacrylonitrile or copolymersof acrylonitrile. These dyestuffs show very good absorption especiallyon structures of linear polyamides, for example polycaprolactam,polyhexamethylenediamine adipate or poly-e-aminoundecane-acid. Theviolet to blue dyeings are distinguished by good light fastness andfastness to wet processing.

Compared to the dyestuffs known from German patent specification1,243,803, the dyestuffs according to the invention show some improveddyeing properties. Thus, for example, the dyestutf of formula obtainableaccording to the invention is distinguished by better fastness to wetprocessing on polyamides, compared to the dyestutf of formula known fromthe abovementioned German patent specification.

In the example which follows, the temperatures quoted are degreescentigrade. The parts mentioned are, unless otherwise stated, parts byweight, and the relationship of parts by volume to parts by weight is asof the litre to the kilogram under normal conditions.

3 EXAMPLE 116 parts of 6-amino-1,3-benzodioxane (manufacture: An. Soc.espafi. 26, 420 (1928)) are stirred with 1000 parts by volume of water,with the addition of 212 parts by volume of 30% strength hydrochloricacid, and cooled to 10 by the addition of 200 parts of ice. 177 parts byvolume of 30% strength sodium nitrite solution are slowly added at10-15" and the mixture is subsequently stirred for one hour at thistemperature.

103 parts of l-amino-naphthalene are dissolved in 2,300 parts by volumeof water and 100 parts by volume of 30% strength hydrochloric acid at 80and reprecipitated in a fine form by adding 1000 parts of ice and 610parts by volume of 20% strength sodium acetate solution. The diazotisedproduct, neutralised with 350 parts by volume of 20% strength sodiumacetate solution, is added, with stirring, to the resulting suspensionat -5 After completion of the coupling, 120 parts by volume of 30%strength hydrochloric acid are added, and the precipitate is filteredoff and washed with water.

The paste of the monoazo dyestuff of Formula II, thus obtained, isstirred with 1,500 parts by volume of ethylene glycol monoethyl etherwith the addition of 200 parts by volume of 30% strength hydrochloricacid. 180 ml. of 30% strength sodium nitrite solution are added at 10 to20". After three hours stirring at approx. 15 the diazotisation iscomplete.

161.5 parts of l-N-(13-hydroxyethylamino)-naphthalene hydrocholride arestirred with 1,500 parts by volume of ethylene glycol monoethyl etherand the diazotised product is added at a temperature of 10-20, whilststirring. The coupling is complete after a short time. The resultingdisazo dyestutf of formula Colour Coupling component shade Blue-NHCH-?H-CH3 violet.

O-GH:

Colour Coupling component shade Do. Q-nm-crn-on-orn-m 5 Q E D0.NH-CH;CHOHrO-CH1 2 H Violet. -NHCHrCHz-Ci-O-OH: 15

Do. @NH-CHr-CH:-fi-OCHzCHz-OCH;

Blue- -NHom-on,-o-cm-om-pn violet.

Do. -NH-orn-on,-on,-cn. Q

Violet.

D0. -Nu-cmon-om-on H Do.

We claim:

1. Disazo dyestuflz' of the formula HzC in which R' is alkyl of 1 to 4carbon atoms; or alkyl of 1 to 4 carbon atoms substituted by alkoxy with1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms,

nitrile, hydroxyl or halogen.

References Cited UNITED STATES PATENTS 3,376,280 4/1968 Gottschlich eta1. 260-152 LEWIS GOTTS, Primary Examiner D. M. PAPUGA, AssistantExaminer US. Cl. X.R.

